WO1998054569A1 - Polymeres marques au luminol pour le traitement de systemes industriels - Google Patents
Polymeres marques au luminol pour le traitement de systemes industriels Download PDFInfo
- Publication number
- WO1998054569A1 WO1998054569A1 PCT/US1998/009918 US9809918W WO9854569A1 WO 1998054569 A1 WO1998054569 A1 WO 1998054569A1 US 9809918 W US9809918 W US 9809918W WO 9854569 A1 WO9854569 A1 WO 9854569A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- luminol
- epichlorohydrin
- monomer units
- tagged
- Prior art date
Links
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
- C08G73/0226—Quaternisation of polyalkylene(poly)amines
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/80—Fluorescent dyes, e.g. rhodamine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/12—Condition responsive control
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/13—Tracers or tags
Definitions
- the present invention relates generally to the treatment and monitoring of industrial systems and, more specifically, to the treatment and monitoring of industrial systems using luminol -tagged polymers in combination with fluorescent or chemiluminescent detection techniques.
- Polymeric coagulants are added to industrial water systems and waste water systems as monitoring agents because technological advances have enabled those skilled in the art to feasibly monitor the residual level of such polymeric coagulant additives.
- Knowledge of the fate of polymeric coagulants in industrial water and waste water systems enables operators to monitor the residual content of the polymeric coagulants and therefore the residual content of other compositions in the water.
- coagulant dosage can be automated.
- a knowledge of the fate of coagulant in a system assists in the diagnosing of treatment difficulties, and potentially, a diagnosing of treatment difficulties before the difficulties reduce in non-conformance treated water.
- the typical approach to monitoring the level of water soluble polymer coagulants in a system has been to blend fluorescent dyes in small amounts and to use the fluorescence of the mixture to determine the concentration of the polymer in the system. While this approach has been relatively successful, it has limitations. Specifically, fluorescent dyes can become associated with other components of the system, such as sample particulates . Accordingly, a subsequent fluorescent detection of the dye may not necessarily provide evidence of the location or detection of the polymeric coagulan .
- the present invention satisfies the aforenoted needs by providing a composition that is capable of being detected in a solution by chemiluminescent techniques as well as fluorescent techniques. More specifically, the present invention provides a polymer tagged with luminol that can be detected even at very low concentrations in a solution utilizing either chemiluminescent or fluorescent techniques. The present invention also provides an improved method for detecting the presence of a substance or composition in a solution.
- the present invention provides a composition capable of being detected in a solution by chemiluminescent or fluorescent detection techniques which comprises a polymer tagged with luminol .
- the polymer comprises epichlorohydrin monomer units.
- the polymer is further characterized as being a copolymer comprising epichlorohydrin monomer units and dimethylamine monomer units .
- the polymer is a copolymer comprising epichlorohydrin monomer units and dimethylamine monomer units with luminol covalently bonded between some of the epichlorohydrin monomer units and dimethylamine monomer units, the luminol being present in the copolymer in an amount ranging from about 0.05% to about 2% by weight.
- a tagged portion of the polymer of the present invention has the following formula:
- the present invention provides a composition comprising epichlorohydrin monomer tagged with luminol .
- the present invention provides the composition comprising a luminol tagged monomer. It is therefore an advantage of the present invention to provide a monomer tagged with chemiluminescent and/or fluorescent chromophore that can be detected in a solution at low concentrations utilizing conventional chemiluminescent or fluorescent detection techniques .
- Another advantage of the present invention is to provide a polymer tagged with chemiluminescent/ fluorescent chromophore such at luminol that can be detected in a solution at low concentrations using conventional chemiluminescent or fluorescent techniques.
- Yet another advantage of the present invention is the ability to tag a polymer with luminol during the condensation polymer reaction resulting in luminol covalently bonded to the polymer.
- Yet another advantage of the present invention is to provide an improved method of tagging a monomer or a polymer with luminol .
- Another advantage of the present invention is to provide an improved method of tagging a monomer or a polymer with luminol .
- Another advantage of the present invention is to provide an improved composition for use in dosage control, residuals monitoring, automated particle sizing control, and in the general treatment of industrial waters .
- Figure 1 illustrates, graphically, the ability of a composition prepared in accordance with the present invention to act as a coagulant while being detectable at low dosages;
- Figure 2 illustrates, graphically, the ability of a composition prepared in accordance with the present invention to provide fluorescent information over a low dosage range
- Figure 3 illustrates, graphically, the correlation of a composition prepared in accordance with the present invention to apparent color removal performance and the non-correlation of a prior art composition to apparent color removal performance.
- DETAILED DESCRIPTION OF THE PRESENTLY PREFERRED EMBODIMENTS The present invention provides an improved composition that can be detected at low concentrations using conventional fluorescent or chemiluminescent detection methods.
- One embodiment of the present invention is luminol tagged epichlorohydrin-dimethylamine polymer.
- Luminol is a chemiluminescent species with its structure being shown below:
- luminol, nile blue and thionine can also be used as chromophores as well.
- a monomer, such as epichlorohydrin can be tagged with a chromophore to provide a composition capable of being detected by fluorescent or chemiluminescent methods at low concentrations in accordance with the present invention.
- the invention comprises copolymers of epichlorohydrin-dimethylamine which contains from 0.05% -
- the invention further contemplates using these polymers in water treating applications such as, but not limited to coagulation. This allows the dosage and residual quantities of the polymers to be controlled and monitored using conventional fluorescence/ chemiluminescent detecting equipment even though the polymers are present in the ppb range.
- the luminol Utilizing the primary aromatic amine group in luminol, the luminol is incorporated into the polymer's backbone.
- the hydrocarbon linkage is essentially a tertiary amine leaving the ring nitrogens available for fluorescent or chemiluminescent applications. It is also theoretically possible to react epichlorohydrin with luminol and then polymerize into the usual epichlorohydrin/dimethylamine reaction, forming essentially the same tagged polymer.
- the luminol and dimethylamine are desirably reacted with the epichlorohydrin at 80°C using general synthetic methods that are known to those skilled in the art .
- the epichlorohydrin polymers modified by luminol may be synthesized using known condensation polymerization techniques.
- the resulting copolymers may contain from about 0.05% to about 2% by weight of the luminol monomer.
- luminol is a monomer and potentially can be incorporated at higher levels.
- the amount of fluorescent monomer is within the range of 0.1% to 1% by weight of the resulting tagged polymer.
- a luminol tagged epichlorohydrin-dimethylamine monomer prepared in accordance with the present invention has an average molecular weight of 10,000 amu versus 20,000 amu for an unmodified epichlorohydrin- dimethylamine polymer. For most water treating applications, such as coagulation, the molecular weight should be less than c.a. 100,000 amu.
- the dosage of the modified polymers should usually vary from a few parts per million (ppm) up to several hundred ppm depending upon the system being treated and the intrinsic viscosity of the polymer in use.
- the dosage When used as a coagulant, the dosage should typically be between a few ppm up to approximately 100 ppm.
- Brookfield viscosity was obtained using a
- composition of the present invention has similar characteristics to untagged epichlorohydrin/dimethylamine polymer. Luminol incorporation was determined analytically.
- Activity testing was performed by testing papermill effluent with fresh and aged luminol -epichlorohydrin/ dimethylamine copolymer. Coagulation power is unchanged. It was noted that the invention is light sensitive and at room temperature, will darken over a six month period. A portion saved in darkness for the same time period at 4°C showed only moderate color change .
- the present invention provides a tagged polymer that is useful in the treatment of industrial waters.
- the tagged polymers made in accordance with the present invention can be used to monitor treated water residuals, control coagulant addition and be used in the analysis of coagulation mechanism.
- the present invention helps to minimize the contribution to pollution attributable to polymeric coagulants.
- the present invention avoids the shortcomings associated with the prior art method of blending fluorescent dyes with polymeric coagulants which, as discussed above, results in a physical separation or disassociation between the dye and coagulant.
- polymers tagged with a chromophore in accordance with the present invention are detectable at low dosage levels.
- the modified or tagged polymer prepared in accordance with the present invention has an activity similar to an unmodified polymer.
Abstract
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002291844A CA2291844A1 (fr) | 1997-05-28 | 1998-05-15 | Polymeres marques au luminol pour le traitement de systemes industriels |
BR9809505-6A BR9809505A (pt) | 1997-05-28 | 1998-05-15 | Composição capaz de ser detectada em uma solução por detecção quimioluminescente ou fluorescente, processo para detecção da presença de uma substância em um sistema, e, copolìmero contendo unidades de monÈmero epicloroidrina e unidades de monÈmero dimetilamina |
EP98921209A EP0985147A1 (fr) | 1997-05-28 | 1998-05-15 | Polymeres marques au luminol pour le traitement de systemes industriels |
JP50073099A JP2002501566A (ja) | 1997-05-28 | 1998-05-15 | 工業的システムにおける処理のためのルミノール標識ポリマー |
KR19997011067A KR20010013088A (ko) | 1997-05-28 | 1998-05-15 | 산업 시스템의 처리에 사용되는 루미놀-태그 폴리머 |
AU73872/98A AU745143B2 (en) | 1997-05-28 | 1998-05-15 | Luminol tagged polymers for treatment of industrial systems |
NO995844A NO995844D0 (no) | 1997-05-28 | 1999-11-29 | Lumino/merkede polymerer for behandling av industrielle systemer |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/864,656 | 1997-05-28 | ||
US08/864,656 US5958788A (en) | 1997-05-28 | 1997-05-28 | Luminol tagged polymers for treatment of industrial systems |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998054569A1 true WO1998054569A1 (fr) | 1998-12-03 |
Family
ID=25343763
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/009918 WO1998054569A1 (fr) | 1997-05-28 | 1998-05-15 | Polymeres marques au luminol pour le traitement de systemes industriels |
Country Status (10)
Country | Link |
---|---|
US (1) | US5958788A (fr) |
EP (1) | EP0985147A1 (fr) |
JP (1) | JP2002501566A (fr) |
KR (1) | KR20010013088A (fr) |
CN (1) | CN1258355A (fr) |
AU (1) | AU745143B2 (fr) |
BR (1) | BR9809505A (fr) |
CA (1) | CA2291844A1 (fr) |
NO (1) | NO995844D0 (fr) |
WO (1) | WO1998054569A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1282732A1 (fr) * | 2000-04-27 | 2003-02-12 | Ondeo Nalco Company | Monomeres fluorescents et polymeres de traitement marques contenant ces monomeres destines aux systemes d'eau industrielle |
WO2009077760A1 (fr) | 2007-12-17 | 2009-06-25 | Lux Innovate Limited | Compositions et procédés pour l'entretien de systèmes d'acheminement et de confinement de fluides |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9425138D0 (en) | 1994-12-12 | 1995-02-08 | Dynal As | Isolation of nucleic acid |
US6358746B1 (en) * | 1999-11-08 | 2002-03-19 | Nalco Chemical Company | Fluorescent compounds for use in industrial water systems |
US20030049850A1 (en) * | 2001-09-12 | 2003-03-13 | Golden Josh H. | Enhanced detection of metal plating additives |
US6662636B2 (en) | 2001-12-13 | 2003-12-16 | Ondeo Nalco Company | Method of reducing fouling in filters for industrial water system analytical devices |
US6790666B2 (en) * | 2001-12-28 | 2004-09-14 | Nalco Company | Method to ascertain whether soluble hardness is calcium or magnesium based |
US6790664B2 (en) * | 2001-12-28 | 2004-09-14 | Nalco Company | Fluorometric monitoring and control of soluble hardness of water used in industrial water systems |
US6812309B2 (en) * | 2002-01-08 | 2004-11-02 | Rohm And Haas Company | Digitally encoded polymers |
EP1468116A2 (fr) | 2002-01-16 | 2004-10-20 | Dynal Biotech ASA | Methode permettant d'isoler des acides nucleiques et des proteines contenus dans un echantillon unique |
GB0229287D0 (en) * | 2002-12-16 | 2003-01-22 | Dna Res Innovations Ltd | Polyfunctional reagents |
US7601789B2 (en) * | 2003-09-09 | 2009-10-13 | Nalco Company | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
US7883898B2 (en) * | 2007-05-07 | 2011-02-08 | General Electric Company | Method and apparatus for measuring pH of low alkalinity solutions |
US20080295581A1 (en) * | 2007-05-31 | 2008-12-04 | General Electric Company | Method for the determination of aqueous polymer concentration in water systems |
US8343771B2 (en) | 2011-01-12 | 2013-01-01 | General Electric Company | Methods of using cyanine dyes for the detection of analytes |
CN102252985A (zh) * | 2011-06-10 | 2011-11-23 | 同济大学 | 氯化频哪氰醇分光光度法测定循环冷却水中聚环氧琥珀酸含量的方法 |
US10358363B2 (en) | 2015-03-17 | 2019-07-23 | Ecolab Usa Inc. | Fluorescent polymers for water treatment |
Citations (5)
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US4788142A (en) * | 1983-08-09 | 1988-11-29 | Toray Industries, Incorporated | Method of assaying the metabolic activity of cells capable of endocytosis |
WO1992013272A1 (fr) * | 1991-01-29 | 1992-08-06 | British Technology Group Ltd | Analyse de polluants presents dans l'eau |
US5171450A (en) * | 1991-03-20 | 1992-12-15 | Nalco Chemical Company | Monitoring and dosage control of tagged polymers in cooling water systems |
US5260386A (en) * | 1990-08-20 | 1993-11-09 | Nalco Chemical Company | Synthesis of tagged polymers by post-polymerization (trans) amidation reaction |
US5705394A (en) * | 1995-04-17 | 1998-01-06 | Nalco Chemical Company | Tagged epichlorohydrin-dimethylamine copolymers for use in wastewater treatment |
Family Cites Families (11)
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US4166105A (en) * | 1973-07-30 | 1979-08-28 | Block Engineering, Inc. | Dye tagged reagent |
US4217262A (en) * | 1977-12-15 | 1980-08-12 | American Cyanamid Company | Preparation of a cationic copolymer |
US4152200A (en) * | 1977-12-15 | 1979-05-01 | American Cyanamid Company | Process for draining formed paper |
JPS58137759A (ja) * | 1982-02-10 | 1983-08-16 | Hitachi Ltd | 免疫学的活性複合体 |
US4783314A (en) * | 1987-02-26 | 1988-11-08 | Nalco Chemical Company | Fluorescent tracers - chemical treatment monitors |
US5003050A (en) * | 1990-03-07 | 1991-03-26 | The United States Of America As Represented By The Secretary Of The Air Force | Diazoluminomelanin and a method for preparing same |
US5128419A (en) * | 1990-08-20 | 1992-07-07 | Nalco Chemical Company | Synthesis of tagged polymers by post-polymerization (trans) amidation reaction |
JP3189307B2 (ja) * | 1991-07-30 | 2001-07-16 | 昭和電工株式会社 | 化学発光検出用充填剤およびそれを用いた分析方法 |
US5413719A (en) * | 1994-01-18 | 1995-05-09 | Nalco Chemical Company | Fluorescent tracer in a water treatment process |
US5435969A (en) * | 1994-03-29 | 1995-07-25 | Nalco Chemical Company | Monitoring water treatment agent in-system concentration and regulating dosage |
US5645799A (en) * | 1995-03-06 | 1997-07-08 | Nalco Chemical Company | Apparatus for a continuous polymer dosage optimization and waste water analysis system |
-
1997
- 1997-05-28 US US08/864,656 patent/US5958788A/en not_active Expired - Lifetime
-
1998
- 1998-05-15 EP EP98921209A patent/EP0985147A1/fr not_active Withdrawn
- 1998-05-15 CN CN98805501A patent/CN1258355A/zh active Pending
- 1998-05-15 WO PCT/US1998/009918 patent/WO1998054569A1/fr not_active Application Discontinuation
- 1998-05-15 AU AU73872/98A patent/AU745143B2/en not_active Ceased
- 1998-05-15 JP JP50073099A patent/JP2002501566A/ja active Pending
- 1998-05-15 BR BR9809505-6A patent/BR9809505A/pt not_active Application Discontinuation
- 1998-05-15 CA CA002291844A patent/CA2291844A1/fr not_active Abandoned
- 1998-05-15 KR KR19997011067A patent/KR20010013088A/ko not_active Application Discontinuation
-
1999
- 1999-11-29 NO NO995844A patent/NO995844D0/no not_active Application Discontinuation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4788142A (en) * | 1983-08-09 | 1988-11-29 | Toray Industries, Incorporated | Method of assaying the metabolic activity of cells capable of endocytosis |
US5260386A (en) * | 1990-08-20 | 1993-11-09 | Nalco Chemical Company | Synthesis of tagged polymers by post-polymerization (trans) amidation reaction |
WO1992013272A1 (fr) * | 1991-01-29 | 1992-08-06 | British Technology Group Ltd | Analyse de polluants presents dans l'eau |
US5171450A (en) * | 1991-03-20 | 1992-12-15 | Nalco Chemical Company | Monitoring and dosage control of tagged polymers in cooling water systems |
US5705394A (en) * | 1995-04-17 | 1998-01-06 | Nalco Chemical Company | Tagged epichlorohydrin-dimethylamine copolymers for use in wastewater treatment |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1282732A1 (fr) * | 2000-04-27 | 2003-02-12 | Ondeo Nalco Company | Monomeres fluorescents et polymeres de traitement marques contenant ces monomeres destines aux systemes d'eau industrielle |
EP1282732A4 (fr) * | 2000-04-27 | 2004-12-22 | Ondeo Nalco Co | Monomeres fluorescents et polymeres de traitement marques contenant ces monomeres destines aux systemes d'eau industrielle |
WO2009077760A1 (fr) | 2007-12-17 | 2009-06-25 | Lux Innovate Limited | Compositions et procédés pour l'entretien de systèmes d'acheminement et de confinement de fluides |
Also Published As
Publication number | Publication date |
---|---|
JP2002501566A (ja) | 2002-01-15 |
NO995844L (no) | 1999-11-29 |
KR20010013088A (ko) | 2001-02-26 |
NO995844D0 (no) | 1999-11-29 |
AU7387298A (en) | 1998-12-30 |
EP0985147A1 (fr) | 2000-03-15 |
BR9809505A (pt) | 2000-06-20 |
CA2291844A1 (fr) | 1998-12-03 |
CN1258355A (zh) | 2000-06-28 |
AU745143B2 (en) | 2002-03-14 |
US5958788A (en) | 1999-09-28 |
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